2-Mercaptoethanol → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamide

HRID 52095

Reaktionsgleichung

Reaktionsgleichung von HRID 52095
[SH:1][CH2:2][CH2:3][OH:4].[OH-].[K+].[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CO>[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:28])[CH2:26][S:1][CH2:2][CH2:3][OH:4])[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

5

Edukt 3

HCID 15672-MercaptoethanolHCID 14797Potassium HydroxideHCID 19962925N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-chloroacetamide

Produkt 1

HCID 19962907N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.12 ml of 2-mercaptoethanol was added to a solution of 0.13 g of 85% potassium hydroxide and 0.50 g of N-[3-(4-piperidinomethyl-2-pyridyloxy)propyl]-2-chloroacetamide [prepared as described in step (a) above] in 10 ml methanol, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, the concentrate was mixed with water, and the resulting aqueous mixture was extracted with chloroform. The extract was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.43 g (yield 77%) of the title compound as an oil.

Aufarbeitung

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. additionthe concentrate was mixed with water
  3. extractionthe resulting aqueous mixture was extracted with chloroform
  4. concentrationThe extract was concentrated by evaporation under reduced pressure
  5. customthe residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethanol and chloroform as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-19df28b2737b4a69a239e6d9146cc7db
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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